The best coastal towns within two hours of Siena
West and south of Siena the clay hills flatten into pinewoods, and the air turns from dust to salt. The coast here is long and low, backed by macchia scrub and umbrella pines, with wide sand rather than the pebble coves of Liguria. Towns sit either on the water or on a rise just behind it, built in dark local stone and pale plaster, with wild boar and pappardelle on the menu inland and grilled sea bream, spaghetti with clams and Vermentino a few kilometres downhill. Late spring and September are the best of it, when the sea is warm, the pinewood shade is cool and the beach clubs have not yet filled.
Most people leaving Siena for salt water aim at the Argentario peninsula, Porto Santo Stefano and the ferries to Giglio, or else at Punta Ala and Follonica in high August. The reasons are obvious: clear water, good sailing, a certain amount of glamour. The reasons it is crowded are equally obvious. Parking becomes a sport in July and August, and the coast road slows to a queue.
The same coastline continues past the marinas in both directions, into the Maremma and up the Etruscan Coast towards Bibbona and Cecina. Behind the beaches sit stone towns on hilltops with the sea in view, wine roads through Bolgheri country, and lagoon towns where flamingos stand in shallow water. Fewer people go to these, which is mostly a matter of habit rather than merit. All of them are on the sea, or within sight and smell of it, and all are within reach of Siena for the day.
Of the 80 communes we have mapped in a 120-minute drive of Siena, 8 qualify as coastal towns: each is on the sea. The smallest, Montescudaio, has 2,144 residents.
Two more lists worth reading alongside this one: A 7-day trip through the Tuscan Maremma, based in Grosseto and The best hidden coastal towns that eat well in Toscana.
Montescudaio
Why visit Montescudaio
Montescudaio sits fifteen kilometers inland from the Tyrrhenian coast, on a hill above the valley the Cecina river cuts toward the sea. Fewer than 2,200 people live in the commune, and most of them are outside the centro storico, which is left as a tight knot of stone houses ringed by its old walls: a single church, the clock tower, and the terrace where the vines drop downhill toward the Val di Cecina and the water beyond.
The town carries four institutional signals at once, an unusual density for its size: a registered wine appellation, a bread-network membership rare in this part of Tuscany, a name that predates the medieval walls, and the walls themselves built around an eleventh-century abbey. Wine and bread are both grown and baked around the same hilltop that once needed fortifying.
The fortress, the loaf, and the vineyard are not three separate stories here but three uses of the same ground, worked over centuries after the shields it was named for stopped being necessary.
What to see in Montescudaio
- Centro storico. Walled medieval village, a tight ring of stone houses on the hilltop, built around the abbey that gave the settlement its first walls and structure.
- Torre Civica. Clock tower at the entrance to the borgo, the tallest visible structure and former civic landmark of the fortified village.
- Chiesa di Santa Maria Assunta. Eleventh-century parish church on the site of the medieval abbey, the anchor around which the walled village took shape.
How to get to Montescudaio
There is no station we could confirm here, so this one means driving. Livorno is roughly 44 minutes away by road.
Our tip
May through September is the season on the Cecina hills: dry days, vine work, harvest from late August through September. The coast lies fifteen kilometers west and the sea breeze keeps evening temperatures lower than the inland Maremma. July and August bring crowds to the beaches at Cecina and Marina di Bibbona, but the borgo on the hill stays quieter.
Bibbona
Why visit Bibbona
Bibbona sits at 85 meters in the Val di Cecina, in the southern province of Livorno, eight kilometers from the sea. The town has Etruscan origins, attested by a small bronze goat statuette, now in the Florence archaeological museum, that became the town symbol.
After medieval struggles between Pisa and Florence, the territory passed to the Gherardesca counts, who controlled most of the Etruscan Coast. Monk-knights, probably French and probably Templar, operated from the pieve in the medieval period, a detail that survives more clearly in local memory than in stone.
The village keeps its hill position while its coastal frazione does the work of meeting the sea: the fort once handled customs, sanitary inspection and defense, the beach now holds a national recognition, and the reserve in the inland hills once supplied the wood that moved through that same coastline. Upper town, shore and forest were never separate economies so much as three faces of one strip of land running from the Val di Cecina down to the sea.
The beach here holds the national bathing award, which a comune has to win back every year on water quality, beach management and safety.
What to see in Bibbona
- Pieve di Sant'Ilario. The church stands on Piazza XX Settembre. The right side and facade keep their Romanesque lines, while the added left nave throws the plan out of square, a visible seam between two building campaigns three centuries apart.
- Borgo medievale. Concentric ring of stone streets and stairways around the old castle, with surviving medieval gates and the central piazza.
- Forte di Marina di Bibbona. Built for customs control, sanitary inspection and defense against corsairs, the fort held a working coastline job, not a decorative one, watching the same shore the beach now occupies.
How to get to Bibbona
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 51 minutes away by road.
Our tip
May and June bring warm water and quiet beaches, before the July and August crowds reach the Costa degli Etruschi. The borgo at 85 meters stays five degrees cooler than the coast and is the place to sleep in high summer. July and August are full: Marina di Bibbona fills, the pine-shaded beach fronts get crowded, and the Forte sees long queues at sunset.
Castiglione della Pescaia
Why visit Castiglione della Pescaia
Castiglione della Pescaia sits at sea level on the Maremma coast, north of Grosseto, with a medieval upper town rising on the promontory above the harbor. The site was Roman Salebrone, before that Etruscan and Umbrian, settled because of the lake behind it that the Romans called Portus Traianus.
The lake silted up over time; what remains of it is the wetland reserve southeast of town, a Ramsar site since 1991. The upper town and the harbor below it read as two halves of one settlement: the fortress watching the water from above, the working port beneath, and behind both the flat reclaimed ground where the lake used to be.
Inland and to the east, the hills hold the remains of one of the major Etruscan cities, apart from the coastal life below. North of town, the pine forest gave Calvino his summers and now holds his grave on the hill above the harbor.
The place is built in layers: a silted lake turned nature reserve, a watchtower turned fortress, an Etruscan hill city, and a modern coastline still shaped by all of it.
The beach here holds the national bathing award, which a comune has to win back every year on water quality, beach management and safety. It is also rated for accessibility, which most of this coast is not.
What to see in Castiglione della Pescaia
- Rocca Aragonese. Castle on the promontory above the harbor, 10th-century watchtower core enlarged by Alfonso of Aragon in the 15th century, modified by Cosimo I and the Lorraine.
- Riserva Naturale Diaccia Botrona. Wetland reserve southeast of town with bird-watching hides, pink flamingos and white herons in season.
- Casa Rossa Ximenes. Hydraulic structure built by Jesuit engineer Leonardo Ximenes for the Lorraine drainage works; now multimedia museum of the wetland reserve.
How to get to Castiglione della Pescaia
There is no station we could confirm here, so this one means driving. Livorno is roughly 113 minutes away by road.
Our tip
May and June bring warm sea and quiet beaches, before the high-summer crowds arrive from Rome and Florence. June through September holds the Bandiera Blu and the Diaccia Botrona stays accessible in the cooler hours. July and August push the coast above thirty; Punta Ala and the harbor fill, and the Rocca above the old town becomes a sunset destination. Palio Marinaro di Castiglione della Pescaia falls in August.
Castagneto Carducci
Why visit Castagneto Carducci
Castagneto Carducci sits at 194 meters on a hill above the Costa degli Etruschi, sixty kilometers south of Livorno. The town was called Castagneto until 1907, when it was renamed for the poet Giosuè Carducci, who spent part of his childhood here and made the surrounding landscape the subject of Davanti a San Guido.
The Castello della Gherardesca, the Lombard-origin fortress of the counts who held the land for nine centuries, still anchors the centro storico. Below the hill, on a coastal plain that locals call the Maremma livornese, sits the frazione of Bolgheri.
In 1944, Mario Incisa della Rocchetta planted Cabernet Sauvignon on his estate there; the resulting wine, Sassicaia, started the category that journalists in the 1970s named Supertuscan. Bolgheri DOC was created in 1983 and Bolgheri Sassicaia DOC in 1994, a sub-zone for a single estate.
The cypress avenue from the coast road up to Bolgheri, two parallel rows planted in 1832, is the one Carducci put in the poem.
The beach here holds the national bathing award, which a comune has to win back every year on water quality, beach management and safety.
What to see in Castagneto Carducci
- Castello della Gherardesca. Lombard-origin fortress at the top of the borgo, held by the Della Gherardesca counts for nine centuries, still in private family use.
- Viale dei Cipressi. Five-kilometer cypress avenue between the SS1 Aurelia and the frazione of Bolgheri, planted in 1832 and immortalized by Carducci.
- Bolgheri. Coastal-plain frazione at 88 meters, walled medieval village turned wine capital, home of Sassicaia, Ornellaia and the Bolgheri DOC.
How to get to Castagneto Carducci
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 55 minutes away by road.
✷ We have written about Castagneto Carducci
“You reach Bolgheri up a straight avenue of cypresses, five kilometers of them standing in two close files like a colonnade with the roof taken off, and the road does the thing it was planted centuries ago to do, which is tell you before you get there that you are arriving somewhere that thinks a great deal of itself. The comune the village belongs to carries its name.”
Read our piece on Castagneto Carducci →Bolgheri | The Story of an Amaro
Our tip
May through September is the season the comune fills, the coast at Marina di Castagneto holds Bandiera Blu, and the Bolgheri cellars run their tastings on appointment. The Bolgheri DiVino wine festival runs in mid-August. July and August push afternoon temperatures past thirty and the cypress avenue stops being walkable in midday sun.
Campiglia Marittima
Why visit Campiglia Marittima
Campiglia Marittima sits at 231 meters on the last slopes of the Colline Metallifere above the Val di Cornia, eight kilometers inland from the Tyrrhenian coast and 60 kilometers southeast of Livorno. The Rocca occupies the highest point at 281 meters, a fortified semicircle whose 14th-century tower and town walls trace the medieval defensive line.
The territory has been mined since the Etruscans: copper, silver, lead and tin from the hills behind town, worked continuously until the last galleries closed in 1976. The Parco Archeominerario di San Silvestro, opened in 1996 on 450 hectares behind the town, centers on Rocca San Silvestro, a tenth and eleventh-century miners' village abandoned in the fourteenth century and excavated since 1984.
Visitors enter through restored galleries on a small electric train. Down on the plain the DOC Val di Cornia produces Sangiovese and Cabernet, and the thermal springs at Venturina, the frazione south of town, have flowed since Roman use as Aquae Populoniae.
What to see in Campiglia Marittima
- Rocca di Campiglia. Fortified semicircle at 281 meters with the 14th-century tower, walls and the Pieve di San Giovanni, the highest point of the town.
- Parco Archeominerario di San Silvestro. 450-hectare park behind town, opened 1996, with restored mining galleries, a small electric train, and the abandoned medieval miners' village of Rocca San Silvestro.
- Centro storico. Walled hilltop borgo of stone houses, with Piazza della Repubblica at its center, the medieval gates Porta a Mare and Porta Fiorentina still intact.
How to get to Campiglia Marittima
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 67 minutes away by road.
✷ We have written about Campiglia Marittima
“That is the thing the young man on the beach did not see, and the man who lives here cannot stop seeing. This is an industrial coast wearing a beach towel. Run it back far enough and the whole of it, the swamp and the steel and the slag and the white water, is one long story about iron, and the holiday is the costume the story put on after the work ran out.”
Read our piece on Campiglia Marittima →The Iron Coast | The Wrong Sea
Our tip
May through September is the season on the Val di Cornia: warm days, sea breezes that climb the hill, harvest of Sangiovese and Vermentino from late August. The beaches at San Vincenzo and Baratti are eight to fifteen kilometers away and pull the day-traffic. July and August are hot and busy on the coast; the borgo on the hill stays a few degrees cooler.
Orbetello
Why visit Orbetello
The isthmus runs out into the lagoon and splits it into two basins, Ponente and Levante. Two sand tombolos close the shape from either side: Giannella to the north, Feniglia to the south, both reaching toward the Monte Argentario promontory and meeting it at either end.
The Etruscans settled the site first, the Romans followed with their colony of Cosa nearby, and centuries later the Spanish took the isthmus as the seat of their coastal enclave, leaving the Governor's Palace on the main square where it still stands. Of the nine Sienese windmills once built out in the water, one remains in place, the only Italian water-and-wind mill of its type still fixed where it was built.
The lagoon that once carried Balbo's flying boats out toward Rio and Chicago now carries a WWF reserve and the nets of a bottarga and eel cooperative working the same waters since 1965. A town built on the water it is named for, held between two arms of sand and one mountain it never quite touches.
The beach here holds the national bathing award, which a comune has to win back every year on water quality, beach management and safety.
What to see in Orbetello
- Duomo di Santa Maria Assunta. Fourteenth-century cathedral with a Gothic travertine façade, rebuilt over an earlier Etruscan-Roman temple foundation.
- Fortificazioni Spagnole. The bastions and the Polveriera Guzman magazine, still standing along the edges of the historic center.
- Laguna di Orbetello. The brackish water splits into two basins and is now a WWF reserve and Ramsar wetland.
How to get to Orbetello
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Roma is roughly 124 minutes away by road.
✷ We have written about Orbetello
“Everyone driving from Florence down to Rome crosses the Maremma without noticing, because there is nothing on that stretch to make them slow down. The hills give out. The cypresses stop. What opens up instead is flat open country, wheat and grass running off to a few low rises, the least Tuscan-looking part of Tuscany, a landscape you would call dull if you were being honest and which most guidebooks solve by leaving out.”
Read our piece on Orbetello →Maremma | The Last Cowboys of Tuscany
Our tip
May through September is when the lagoon and the Feniglia and Giannella beaches do their work. June brings the migratory bird count back up: flamingos, herons, avocets. July and August push temperatures over thirty degrees and the tombolos fill with Roman day-trippers, so the lagoon path on the Ponente side stays the quieter option. Sagra del Pesce di Albinia falls in the season.
Piombino
Why visit Piombino
Piombino sits on a triangular promontory pointing southeast into the Tyrrhenian, at the northern edge of the Maremma. The town was founded in the ninth century by refugees from the Etruscan port after Greek pirates attacked the city; they called the new settlement Populino, small Populonia, and the name shortened over time to what it is now.
The old city, now a frazione north on the coast, became the source of the newer town's name rather than the other way round. In the medieval period Piombino became an independent signoria under the Appiani, who ruled from here over a small state that reached out to the islands across the water.
The castle at the seafront, the piazza cantilevered out over the cliff toward Elba, and the working ferry port make up the contemporary town, each looking the same direction the refugees once looked back from: toward the older settlement to the north and the channel to the islands beyond it. The Bandiera Blu coast covers the four kilometers between the port and the old acropolis, so that the walk from new town to old runs along the same shoreline that separates them by name only.
The beach here holds the national bathing award, which a comune has to win back every year on water quality, beach management and safety.
What to see in Piombino
- Castello di Piombino. Principal defensive fortress of the city on a headland pointing southeast into the sea, with the Torrione, the Rivellino and the Cittadella complex, now a museum.
- Piazza Bovio. Long rocky breakwater extending into the sea as La Rocchetta, terraced as a piazza, with a balcony view across the channel to Elba.
- Parco Archeologico di Baratti e Populonia. Chamber tombs from the seventh to second centuries BC cut into the ground of the Gulf of Baratti, laid out for walking among the excavated structures rather than viewed from a distance.
How to get to Piombino
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 77 minutes away by road.
Our tip
May, June, September and October are the months when the Piombino promontory is at its best, sea warm enough to swim and the ferry to Elba running every hour without the August crush. July and August are full season, with the centro storico filling by late morning and the Baratti beach turning over twice a day. November through March is cold and windy on the promontory, with limited ferry crossings and many seaside trattorie closed. Sagra del Pesce - Piombino falls in July.
Grosseto
Why visit Grosseto
Grosseto sits on the right bank of the Ombrone, ten meters above sea level and twelve kilometers inland from the Tyrrhenian. The Roman city of Roselle was destroyed in 935 by Saracen pirates; refugees regrouped on the plain below and Grosseto inherited the bishopric.
From 1336 it was Sienese; in 1559 it passed to the Medici after the battle of Montalcino. Cosimo I commissioned Baldassarre Lanci to replace the medieval walls with a hexagonal bastioned circuit, begun in 1565 and finished a decade later.
The walls are intact. Six bastions, two main gates, a continuous earthwork four kilometers around, now planted and used as the city's promenade.
Inside, the Duomo di San Lorenzo holds a Romanesque-Gothic façade in alternating white and pink marble. The Cassero Senese, the Sienese fortress of 1345 swallowed into the later Medici walls, anchors the southeast corner.
Grosseto is the largest city of southern Toscana and the working capital of the Maremma.
The beach here holds the national bathing award, which a comune has to win back every year on water quality, beach management and safety.
What to see in Grosseto
- Mura Medicee. Hexagonal bastioned circuit commissioned by Cosimo I in 1564, designed by Baldassarre Lanci, intact and walkable for the full four kilometers.
- Duomo di San Lorenzo. Thirteenth-century cathedral with a façade in alternating white and pink marble, Latin-cross plan, semicircular apse over the nave.
- Cassero Senese. Travertine-clad Sienese fortress completed in 1345, incorporated into the southeast corner of the Medici walls, now used for exhibitions.
How to get to Grosseto
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 110 minutes away by road.
Our tip
May, September and October are the Maremma months. The walls and the Parco Regionale are open without the heat, the umbrella pines hold their shade, and the wild horses are visible at dawn near the Ombrone mouth. July and August push past thirty-five degrees and the city empties between one and six in the afternoon.
More from Anywhere Italy
- A 7-day trip through the Tuscan Maremma, based in Grosseto
- The best hidden coastal towns that eat well in Toscana
The 7 best coastal towns in the province of Livorno- The best hidden coastal towns you can reach by train in Toscana
- The best towns with a serious restaurant that eat well within 90 minutes of Livorno
The best wine towns within two hours of Pisa